#------------------------------------------------------------------------------
#$Date: 2024-03-05 22:44:32 +0200 (Tue, 05 Mar 2024) $
#$Revision: 290338 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/30/2023021.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2023021
loop_
_publ_author_name
'Rharmili, Nohaila'
'Abdellaoui, Omar'
'Ouazzani Chahdi, Fouad'
'Mague, Joel T.'
'Hökelek, Tuncer'
'Mazzah, Ahmed'
'Kandri Rodi, Youssef'
'Sebbar, Nada Kheira'
_publ_section_title
;
 Crystal structure, Hirshfeld surface analysis, crystal voids,
 inter-action energy calculations and energy frameworks, and DFT
 calculations of 1-(4-methyl-benz-yl)in-do-line-2,3-dione.
;
_journal_coeditor_code           JP2002
_journal_issue                   'Pt 2'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              232
_journal_page_last               239
_journal_paper_doi               10.1107/S2056989024000756
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C16 H13 N O2'
_chemical_formula_moiety         'C16 H13 N O2'
_chemical_formula_sum            'C16 H13 N O2'
_chemical_formula_weight         251.27
_chemical_name_systematic
;
1-(4-Methylbenzyl)indoline-2,3-dione
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/1
_cell_angle_alpha                90
_cell_angle_beta                 94.118(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.6126(4)
_cell_length_b                   4.8680(3)
_cell_length_c                   38.924(2)
_cell_measurement_reflns_used    9960
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32.566
_cell_measurement_theta_min      3.088
_cell_volume                     1249.73(13)
_computing_cell_refinement
;
SAINT (Bruker, 2021)
;
_computing_data_collection
;
APEX4 (Bruker, 2021)
;
_computing_data_reduction
;
SAINT (Bruker, 2021)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
SHELXTL (Bruker, 2021)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Bruker D8 QUEST PHOTON 3'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 3'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       60
_diffrn_reflns_limit_l_min       -59
_diffrn_reflns_number            41604
_diffrn_reflns_theta_full        33.300
_diffrn_reflns_theta_max         33.336
_diffrn_reflns_theta_min         2.098
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.50
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.373
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.028
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.220
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         4846
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0538
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0500P)²+0.4692P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1231
_refine_ls_wR_factor_ref         0.1368
_reflns_number_gt                3359
_reflns_number_total             4846
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jp2002sup1.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2023021.cif.'
_cod_original_cell_volume        1249.74(13)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2023021
_cod_database_fobs_code          2023021
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.968
_shelx_estimated_absorpt_t_max   0.998
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.83652(16) 1.2777(2) 0.62976(3) 0.0407(3) Uani d 1 . .
O O2 1.08789(14) 1.0379(2) 0.68782(3) 0.0388(2) Uani d 1 . .
N N1 0.60620(15) 0.9544(2) 0.64653(3) 0.0256(2) Uani d 1 . .
C C1 0.78827(17) 0.7578(2) 0.69329(3) 0.0252(2) Uani d 1 . .
C C2 0.82166(19) 0.5820(3) 0.72105(3) 0.0288(2) Uani d 1 . .
H H2 0.946524 0.584733 0.734737 0.035 Uiso calc 1 . .
C C3 0.6679(2) 0.4016(3) 0.72839(3) 0.0303(3) Uani d 1 . .
H H3 0.686776 0.278853 0.747327 0.036 Uiso calc 1 . .
C C4 0.48593(19) 0.4006(3) 0.70795(3) 0.0286(2) Uani d 1 . .
H H4 0.382752 0.274792 0.713208 0.034 Uiso calc 1 . .
C C5 0.45014(18) 0.5784(3) 0.67999(3) 0.0258(2) Uani d 1 . .
H H5 0.324978 0.576843 0.666387 0.031 Uiso calc 1 . .
C C6 0.60429(17) 0.7564(2) 0.67298(3) 0.0234(2) Uani d 1 . .
C C7 0.78645(19) 1.0935(3) 0.64820(3) 0.0291(2) Uani d 1 . .
C C8 0.91639(18) 0.9665(3) 0.67911(3) 0.0288(3) Uani d 1 . .
C C9 0.43199(19) 1.0233(3) 0.62289(3) 0.0286(2) Uani d 1 . .
H H9A 0.461089 1.195878 0.610731 0.034 Uiso calc 1 . .
H H9B 0.312938 1.056262 0.636366 0.034 Uiso calc 1 . .
C C10 0.37999(19) 0.8018(3) 0.59657(3) 0.0266(2) Uani d 1 . .
C C11 0.1851(2) 0.6927(3) 0.59296(3) 0.0335(3) Uani d 1 . .
H H11 0.086091 0.753530 0.607771 0.040 Uiso calc 1 . .
C C12 0.1334(2) 0.4962(3) 0.56801(4) 0.0364(3) Uani d 1 . .
H H12 -0.000569 0.424591 0.565979 0.044 Uiso calc 1 . .
C C13 0.2747(2) 0.4027(3) 0.54597(3) 0.0337(3) Uani d 1 . .
C C14 0.4703(2) 0.5080(3) 0.55005(3) 0.0339(3) Uani d 1 . .
H H14 0.570145 0.443987 0.535606 0.041 Uiso calc 1 . .
C C15 0.5222(2) 0.7055(3) 0.57492(3) 0.0305(3) Uani d 1 . .
H H15 0.656602 0.775497 0.577128 0.037 Uiso calc 1 . .
C C16 0.2171(3) 0.1907(3) 0.51890(4) 0.0460(4) Uani d 1 . .
H H16A 0.120928 0.270980 0.501370 0.069 Uiso calc 1 . .
H H16B 0.154047 0.033158 0.529600 0.069 Uiso calc 1 . .
H H16C 0.338779 0.129939 0.508103 0.069 Uiso calc 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 N1 C6 . . 110.91(10) ?
C7 N1 C9 . . 124.13(11) ?
C6 N1 C9 . . 124.65(10) ?
C2 C1 C6 . . 121.38(11) ?
C2 C1 C8 . . 131.50(11) ?
C6 C1 C8 . . 107.12(11) ?
C1 C2 C3 . . 118.28(11) ?
C1 C2 H2 . . 120.9 ?
C3 C2 H2 . . 120.9 ?
C2 C3 C4 . . 119.96(12) ?
C2 C3 H3 . . 120.0 ?
C4 C3 H3 . . 120.0 ?
C3 C4 C5 . . 122.23(12) ?
C3 C4 H4 . . 118.9 ?
C5 C4 H4 . . 118.9 ?
C6 C5 C4 . . 117.18(11) ?
C6 C5 H5 . . 121.4 ?
C4 C5 H5 . . 121.4 ?
C5 C6 C1 . . 120.98(11) ?
C5 C6 N1 . . 128.22(11) ?
C1 C6 N1 . . 110.80(10) ?
O1 C7 N1 . . 127.83(12) ?
O1 C7 C8 . . 126.45(12) ?
N1 C7 C8 . . 105.72(10) ?
O2 C8 C1 . . 130.74(13) ?
O2 C8 C7 . . 123.82(12) ?
C1 C8 C7 . . 105.44(10) ?
N1 C9 C10 . . 113.23(10) ?
N1 C9 H9A . . 108.9 ?
C10 C9 H9A . . 108.9 ?
N1 C9 H9B . . 108.9 ?
C10 C9 H9B . . 108.9 ?
H9A C9 H9B . . 107.7 ?
C15 C10 C11 . . 118.21(12) ?
C15 C10 C9 . . 121.45(11) ?
C11 C10 C9 . . 120.33(12) ?
C12 C11 C10 . . 120.87(13) ?
C12 C11 H11 . . 119.6 ?
C10 C11 H11 . . 119.6 ?
C11 C12 C13 . . 121.00(13) ?
C11 C12 H12 . . 119.5 ?
C13 C12 H12 . . 119.5 ?
C12 C13 C14 . . 118.03(12) ?
C12 C13 C16 . . 120.64(13) ?
C14 C13 C16 . . 121.32(14) ?
C15 C14 C13 . . 121.06(13) ?
C15 C14 H14 . . 119.5 ?
C13 C14 H14 . . 119.5 ?
C10 C15 C14 . . 120.81(12) ?
C10 C15 H15 . . 119.6 ?
C14 C15 H15 . . 119.6 ?
C13 C16 H16A . . 109.5 ?
C13 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C13 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 . 1.2094(16) ?
O2 C8 . 1.2110(15) ?
N1 C7 . 1.3684(16) ?
N1 C6 . 1.4108(15) ?
N1 C9 . 1.4610(15) ?
C1 C2 . 1.3835(17) ?
C1 C6 . 1.4026(16) ?
C1 C8 . 1.4567(18) ?
C2 C3 . 1.3886(18) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.3943(17) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.3973(17) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.3798(17) ?
C5 H5 . 0.9500 ?
C7 C8 . 1.5555(18) ?
C9 C10 . 1.5098(17) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 C15 . 1.3886(18) ?
C10 C11 . 1.3917(18) ?
C11 C12 . 1.388(2) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.390(2) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.390(2) ?
C13 C16 . 1.5040(19) ?
C14 C15 . 1.3895(18) ?
C14 H14 . 0.9500 ?
C15 H15 . 0.9500 ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C4 H4 O2 1_445 0.95 2.41 3.2192(16) 142 y
C9 H9A Cg3 1_565 0.99 2.61 3.4936(15) 148 y
C9 H9B O2 1_455 0.99 2.58 3.5208(17) 158 yes
C16 H16B Cg3 1_545 0.98 2.85 3.5685(16) 131 y
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 0.24(18) ?
C8 C1 C2 C3 . . . . -179.89(12) ?
C1 C2 C3 C4 . . . . 0.10(19) ?
C2 C3 C4 C5 . . . . -0.5(2) ?
C3 C4 C5 C6 . . . . 0.58(18) ?
C4 C5 C6 C1 . . . . -0.23(17) ?
C4 C5 C6 N1 . . . . -179.90(11) ?
C2 C1 C6 C5 . . . . -0.17(18) ?
C8 C1 C6 C5 . . . . 179.93(11) ?
C2 C1 C6 N1 . . . . 179.55(11) ?
C8 C1 C6 N1 . . . . -0.35(13) ?
C7 N1 C6 C5 . . . . 179.35(12) ?
C9 N1 C6 C5 . . . . 5.62(19) ?
C7 N1 C6 C1 . . . . -0.34(14) ?
C9 N1 C6 C1 . . . . -174.07(11) ?
C6 N1 C7 O1 . . . . -178.98(13) ?
C9 N1 C7 O1 . . . . -5.2(2) ?
C6 N1 C7 C8 . . . . 0.84(13) ?
C9 N1 C7 C8 . . . . 174.60(11) ?
C2 C1 C8 O2 . . . . 1.2(2) ?
C6 C1 C8 O2 . . . . -178.96(14) ?
C2 C1 C8 C7 . . . . -179.07(13) ?
C6 C1 C8 C7 . . . . 0.82(13) ?
O1 C7 C8 O2 . . . . -1.4(2) ?
N1 C7 C8 O2 . . . . 178.78(12) ?
O1 C7 C8 C1 . . . . 178.80(13) ?
N1 C7 C8 C1 . . . . -1.02(13) ?
C7 N1 C9 C10 . . . . 114.84(13) ?
C6 N1 C9 C10 . . . . -72.24(15) ?
N1 C9 C10 C15 . . . . -55.98(16) ?
N1 C9 C10 C11 . . . . 125.40(13) ?
C15 C10 C11 C12 . . . . -1.03(19) ?
C9 C10 C11 C12 . . . . 177.63(12) ?
C10 C11 C12 C13 . . . . 0.1(2) ?
C11 C12 C13 C14 . . . . 1.1(2) ?
C11 C12 C13 C16 . . . . -179.70(13) ?
C12 C13 C14 C15 . . . . -1.4(2) ?
C16 C13 C14 C15 . . . . 179.46(13) ?
C11 C10 C15 C14 . . . . 0.78(19) ?
C9 C10 C15 C14 . . . . -177.87(12) ?
C13 C14 C15 C10 . . . . 0.4(2) ?
